Ethanolamine → HCID 86671400, compound

HRID 2403306Notes

Reaction equation

HRID 2403306 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[CH2:11][O:10]2)=[CH:4][N:3]=1.[NH2:12][CH2:13][CH2:14][OH:15].CCOC(C)=O.C1COCC1>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH:9]([OH:10])[CH2:11][NH:12][CH2:13][CH2:14][OH:15])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 21939870Tetrahydrofuran ethyl acetateHCID 86671399HCID 86671399, compound

Product 1

HCID 86671400HCID 86671400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-bromo-3-methyl-5-(oxiran-2-yl)pyridine (1.4 g) in THF (6 ml) was added 2-aminoethanol (3.92 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into EtOAc/THF (1:1) and the mixture was washed with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-1-(6-bromo-5-methylpyridin-3-yl)-2-(2-hydroxyethylamino)ethanol (1.76 g) as an off-white solid which was used in the next step without further purification. MS (ISP): 277.0 ([{81Br}M+H]+), 275.0 ([{79Br}M+H]+), 258.9 ([{81Br}M+H—H2O]+), 257.0 ([{79Br}M+H—H2O]+).

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04afb684bb3740438b82a633efd1380d
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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